Japan · Maldives · Tanzania · Rhine
One big trip a year, planned properly and a long way ahead. Japan is live and being built; the other three carry what research has already turned up so it doesn't get lost.
Sixteen days — Tokyo, an Osaka base for Kansai, and a two-day Seoul stop on the way home. Late October into early November.
In planning · routes, links and budget ready 2028Seven nights on the Rhine, Amsterdam to Basel, with three days in Amsterdam first. Line, cabin and budget worked out; river and air cabin still open.
In planning · two decisions left 2029Seven nights on safari and two on Zanzibar, all-inclusive. Camp tiers and migration timing worked out; the property and the budget still open.
In planning · budget not set 2030An overwater villa on Hilton points. Four Hilton properties now put overwater villas on standard awards — from 120,000 a night, which is cheaper than we assumed.
In planning · 900k points ring-fencedTwo currencies, both spoken for, and one rule that decides where they go.
| Currency | Balance | Earmarked for |
|---|---|---|
| Hilton Honors | ~1.2M | 900,000 held for the Maldives overwater villa. The rest stays banked — in Japan the weak yen has cut cash rates while award prices haven't followed, so most Hilton properties there return well under a cent per point. |
| Chase Ultimate Rewards | ~360k | Japan 2027 flights via Virgin Atlantic at 1:1. Delta One on a fixed partner chart, four one-ways for two people. |
A point is worth what it saves against what you'd otherwise have booked, not against the rack rate. A $1,000 hotel night redeemed when you'd have happily paid $280 saves you $280, not $1,000. So points go where there is no acceptable cash substitute — an overwater villa you'd otherwise skip entirely, a business-class seat you wouldn't buy at $4,000 — and cash covers everything with a good cheaper alternative.
Which is why the Maldives balance is untouchable and Japan's hotels are paid for in cash, even though Japan is the trip happening first.
